Key West Sailing Trips

Key West Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips

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Champagne Celebration Sunset Cruise

5 star rating: Highly Recommended 37 Reviews

Get out on Key West’s beautiful Atlantic waters to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are Chandon Brut ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $79.49

Shipwreck Snorkel and Wild Dolphin Encounter

4.5 star rating: Recommended 19 Reviews

Spend a beautiful Florida day out in the clear, blue waters off Key West. On the Key West Shipwreck Snorkel and Wild Dolphin Encounter cruise, you’ll spot ...  Read more

Location: Key West, Florida
Duration: 4 hours (approx.)

From USD $95.59

Wind and Wine Sunset Sail

Cruise into the sunset with wines from all around the world, Import and Domestic beers and Hors d'euvres. This cruise is great for a romantic evening or just ...  Read more

Location: Key West, Florida
Duration: 2 hours (approx.)

From USD $79.99

Premium Full Day Excursion in Key West

This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing! You will head way back into the Key ...  Read more

Location: Key West, Florida
Duration: 6 hours 30 minutes (approx.)

From USD $109.99

Morning and Afternoon Half Day Cruise

Don't miss one of the top things to do in Key West! Come enjoy the Florida Keys on this kayaking, snorkeling and sailing adventure. You will cruise out to the ...  Read more

Location: Key West, Florida
Duration: 4 hours 30 minutes (approx.)

From USD $79.99

Only Show: Day Cruises | Dolphin & Whale Watching | Night Cruises | Sailing Trips

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